New NHC- silver and gold complexes active in A3-coupling (aldehyde-alkyne-amine) reaction

Mariconda, Annaluisa; Sirignano, Marco; Costabile, Chiara; Longo, Pasquale

doi:10.1016/j.mcat.2019.110570

Cited by 35 publications

(55 citation statements)

References 42 publications

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“…Silver complexes ( 61, 62 ) with N‐methyl‐N′‐(2‐hydroxy‐2‐phenyl) ethyl substituted NHC ligands were synthetized and their catalytic activities in A3‐coupling (aldehyde–alkyne–amine) reactions were compared by Mariconda et al (Figure 20) (Mariconda et al, 2020). DFT studies were done for the understanding of different catalytic activities, electronic and steric properties of the complexes.…”

Section: Methodsmentioning

confidence: 99%

“…Mulliken analysis disclosed a lower positive density charge for complexes with hydrogen NHC substituted complex 61 compared to the complexes with chlorine NHC substituted complex 62 and BDE analysis points out a weaker σ donation of chlorine substituted NHCs toward the metal. In consideration of DFT calculations, results indicated the higher activity of chlorine substituted complex 62 as a result of more electrophile metal center, that easily organize nucleophiles such as alkynes at the very beginning of the catalytic cycle (Mariconda et al, 2020).…”

Section: Methodsmentioning

confidence: 99%

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Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

Şahin‐Bölükbaşı

Cantürk-Kılıçkaya

Kılıçkaya

2021

Drug Development Research

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Because of the continuous need for efficient therapeutic agents against various kinds of cancers and infectious diseases, the pharmaceutical industry has to find new candidates and strategies to develop novel and efficient drugs. They increasingly use computational tools in R&D stages for screening extensive sets of drug candidates before starting pre‐clinical and clinical trials. N‐Heterocyclic carbenes (NHCs) can be evaluated as good drug candidates because they offer both anti‐cancer and anti‐inflammatory features with their general low‐toxicity profiles. To date, different kinds of NHCs (Cu, Co, Ni, Au, Ag, Ru, etc.) have been synthesized and their therapeutic uses has been shown. Here, we have reviewed the recent studies focused on Ag(I)‐NHC complexes and their anti‐cancer activities. Also, existing examples of the usage of density functional theory and structure–activity relationship have been evaluated.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

Şahin‐Bölükbaşı

Cantürk-Kılıçkaya

Kılıçkaya

2021

Drug Development Research

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“…On the bases of these considerations, in this paper we report the synthesis and the biological evaluation of four new coinage complexes with N- [4-(hydroxymethyl) [di-iodide-silver] − (AgL7) and bis-[4,5-dichloro-(N-methyl-N'(2-hydroxy-2-phenyl)ethyl-imidazole-2-ylidene]gold(I)] + [dichloro-gold] − (AuL7) (see Figure 2), whose synthesis has been recently reported [12].…”

Section: Introductionmentioning

confidence: 99%

“…Thus, these results highlighted that AuL7 can be considered a promising lead agent useful for future investigation that could allow the development of new multi-targets agents in cancer treatment. [dichloro-gold] − (AuL7) (see Figure 2), whose synthesis has been recently reported [12]. The anti-tumor activity of all these complexes was evaluated on two breast carcinoma cell lines, MCF-7 and MDA-MB-231, and on two uterine carcinoma cell lines (HeLa and ISHIKAWA).…”

Section: Introductionmentioning

confidence: 99%

Is the Way to Fight Cancer Paved with Gold? Metal-Based Carbene Complexes with Multiple and Fascinating Biological Features

et al. 2020

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Herein, we report the synthesis and the multiple anti-tumor properties of new gold and silver carbene complexes. The chemical modifications, grounded on our previous studies, led us to identify a good lead complex, gold-based, whose biological features are very exciting and promising in the anti-cancer research and could be further developed. Indeed, the bis-[4,5-dichloro-(N-methyl-N’(2-hydroxy-2-phenyl)ethyl-imidazole-2-ylidene)gold(I)]+[dichloro-gold]− (AuL7) complex possesses the ability to interfere with at least three important and different intracellular targets, namely the human topoisomerases I and II and tubulin, which are able to modulate metabolic processes not directly correlated each other. We proved that the modifications of the ligands structure in AuL7, with respect to another already published complex, i.e., bis-[4,5-dichloro-(N-methyl-N’(cyclopentane-2ol)-imidazole-2-ylidine)gold(I)]+[dichloro-gold]− (AuL4), produce a different behavior toward tubulin-polymerization process, since AuL7 is a tubulin-polymerization inhibitor and AuL4 a stabilizer, with the final same result of hampering the tumor growth. Taken together, our outcomes designate AuL7 as a promising compound for the development of multi-targeted anti-cancer therapies.

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“…Efficient catalysts based on N‐heterocyclic carbene complexes of coinage metals have been developed during past few years. [ 28–37 ] Copper‐based catalysts because of natural abundance of copper metal and high reactivity have also attracted great attention. [ 38 ]…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic thiolates and phosphine ligands in copper‐catalyzed synthesis of propargylamines in water

Neshat

Gholinejad

Afrasi

et al. 2021

Applied Organom Chemis

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The product obtained by reaction of deprotonation of 2‐mercaptobenzothiazole or methimazole (2‐mercapto‐1‐methylimidazole) with copper iodide in the presence of tertiary phosphines, PR2R' (R = R' = cyclohexyl; R = R' = phenyl; R = phenyl, R' = methyl) showed high catalytic activity in A3 coupling of a series of aldehydes with phenylacetylene and piperidine, yielding propargylamines. An investigation into the nature of active species carried out mainly by electrospray ionization mass spectrometry (ESI‐MS) techniques underscores a crucial role played by organosulfur and organophosphorus compounds in the generation of active species responsible for these reactions. The coupling reactions were successfully carried out at low catalyst loadings in water/THF (20:1) and in relatively short reaction times. The scope of the reaction was also investigated with 20 examples.

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New NHC- silver and gold complexes active in A3-coupling (aldehyde-alkyne-amine) reaction

Cited by 35 publications

References 42 publications

Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

Silver(I)‐N‐heterocyclic carbene complexes challenge cancer; evaluation of their anticancer properties and in silico studies

Is the Way to Fight Cancer Paved with Gold? Metal-Based Carbene Complexes with Multiple and Fascinating Biological Features

Heterocyclic thiolates and phosphine ligands in copper‐catalyzed synthesis of propargylamines in water

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